Pistachio peel biomass derived magnetic nanoparticles Fe3O4@C-SO3H: a highly efficient catalyst for the synthesis of isoxazole-5(4H)-one, 1-amido alkyl-2-naphthol, pyrano[2,3-c]pyrazole and 2,3-dihydro quinazoline-4(1H)-one derivatives
محورهای موضوعی : Iranian Journal of Catalysis
Fatemeh Ghorbani
1
,
Seied Ali Pourmousavi
2
1 - School of Chemistry, Damghan University Damghan, Iran
2 - School of Chemistry, Damghan University Damghan, Iran|Institute of Biological Science, Damghan University Damghan, Iran
کلید واژه: biomass, pistachio peel, Magnetic nanocatalyst, Isoxazole, amido alkylnaphthol, pyrano pyrazole, dihydro quinazolin,
چکیده مقاله :
Green chemistry has fostered research on recyclable, insoluble, and easily separable heterogeneous catalysts. Carbon materials are widely used for renewable energy and environmental studies. Here, we used green Pistachio peel, a biomass waste for the synthesis of magnetic carbon-based solid acid (Fe3O4@C-SO3H) by carbonization and sulfonation. The physicochemical properties of the nanocatalyst were characterized using XRD, FT-IR, FE-SEM, TGA, VSM, and TEM. The catalytic activity of Fe3O4@C-SO3H was investigated in the synthesis of isoxazole-5(4H)-one, 1-amido alkyl-2-naphthol, pyrano[2,3-c]pyrazole, and 2,3-dihydro quinazoline-4(1H)-one derivative, and some of the synthesized compounds were screened for their anti-microbial activity. Furthermore, the recovery and reuse of the catalyst were demonstrated six times without detectible loss inactivity. The concentration of H+ loaded on the Fe3O4@C-SO3H was reported to be 1.3 mmol g-1. The well-defined Fe3O4@C-SO3H core–shell heterostructures exhibited high stability, efficient recyclability (6 cycles).
[1]. N. Poomathi, S. Mayakrishnan, D. Muralidharan, R. Srinivasan, P.T. Perumal, Green Chem. 17, (2015) 3362-3372.
[2]. E. Ruijter, R. Scheffelaar, R.V.A. Orru, Angew. Chem. Int. Ed. 50, (2011) 6234-6246.
[3]. H. Kiyani, F. Ghorbani, J. Saudi Chem. Soc. 18, (2014) 689.-701
[4]. S. P. N. Sudhan, R. Nasir Ahmed, H. Kiyani, S. Sheik Mansoor, J. Saudi Chem. Soc. 22, (2018) 269-278.
[5]. H. Kiyani, Curr. Org. Synth. 15, (2018) 1043-1052.
[6]. Y. Gu, W. Huang, S. Chen, X. Wang, Org. Lett. 14, (2018) 4285-4293.
[7]. J. Xu, W. Huang, R. Bai, Y. Queneau, F. Jérôme, Y. Gu, Green Chem. 21, (2019) 2061-2069.
[8]. N. Agrawal, P. Mishra, Med. Chem. Res. 27, (2018) 1309-1321.
[9]. S. S. Wazalwar, A. R. Banpurkar, F. Perdih, J. Mol. Struct. 1150, (2017) 258.-267
[10]. A.R. Banpurkar, S.S. Wazalwar, F. Perdih, Bull. Chem. Soc. Ethiop. 32, (2018) 249.-257
[11]. S. J. Kim, J. Yang, S. Lee, C. Park, D. Kang, J. Akter, S. Ullah, Y. J. Kim, P. Chun, H. R. Moon, Bioorg. Med. Chem. 26, (2018) 3882-3889.
[12]. M. Lavanya, M. Jagadeesh, J. Hari Babu, R. Karvembu, H.K. Rashmi, P. Uma Maheswari Devi, A.V. Reddy, Inorganica Chimica Acta 469, (2018) 76-86.
[13]. B. Kafle, H. Cho, Bull. Korean Chem. Soc. 33, (2012) 275-277.
[14]. Y. Kazui, S. Fujii, A. Yamada, M. Ishigami-Yuasa, H. Kagechik, A. Tanatani, Bioorg. Med. Chem. 26, (2018) 5118.-5121
[15]. M. Tang, S. I. Odejinmi, Y. M. Allette, H. Vankayalapati, K. Lai, Bioorg. Med. Chem. 19, (2011) 5886.-5895
[16]. S. Breuer, M. W. Chang, J. Yuan, B. E. Torbett, J. Med. Chem. 55, (2012) 4968-4977.
[17]. Ş. G. Kömürcü, S. Rollas, N. Yilmaz, A. Çevikbaş, Drug Metabol. Drug Interact. 12, (1995) 161-166.
[18]. W. Hallenbach, O. Guth, T. Seitz, H. J. Wrolowsky, P. Desbordes, U. Wachendorff-Neumann, P. Dahmen, E. Voerste, P. Lösel, O. Malssm, R. Rama, H. Hadano, US Patent, Pub. No.: US 2012/0065063A1 (2012).
[19]. A. H. Reshak, S. Azam, Mater. Sci. Semicond. Process. 30, (2015) 197-207.
[20]. A. F. da Silva, A. A. G. Fernandes, S. Thurow, M. L. Stivanin, I. D. Jurberg, Synthesis 50, (2018) 2473-2489.
[21]. T. Ghosh, A. Gopal, A. Saeki, S. Sekic, V. C. Nair, Phys. Chem. Chem. Phys. 17, (2015) 10630-10639.
[22]. H. Kiyani, F. Ghorbani, J. Saudi Chem. Soc. 21, (2017) S112.-S119
[23]. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, (2015) 7847-7882.
[24]. H. Kiyani, M. Jabbari, A. Mosallanezhad, Jordan J. Chem. 9, (2014) 279-284.
[25]. F. Ghorbani, H. Kiyani, S. A. Pourmousavi, Res. Chem. Intermed. 46, (2020) 943–959.
[26]. I. Mohanram, Meshram, J. Med. Chem. Res. 23, (2014) 939.
[27]. H. Darbandi, H. Kiyani, Curr. Organocatal. 7, (2020) 34-48.
[28]. Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose, S. Shirato, J. Antibiot. 25, (1972) 44.-47
[29]. J. L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot, M. Millan, Bioorg. Med. Chem. Lett. 7, (1997) 881-886.
[30]. G. Y. Lesher, A. R. Surrey, J. Am. Chem. Soc. 77, (1955) 636-647.
[31]. M. Karabacak, M. Kurt, J. Mol. Struct. 919, (2009) 215-222.
[32]. S. A. Pourmousavi, P. Moghimi, F. Ghorbani, M. Zamani, J. Mol. Struct. 1144, (2017) 87-102.
[33]. A. V. Shelke, B. Y. Bhong, N. N. Karade, Synthesis 46, (2014) 752-789.
[34]. G. Y. Lesher, A. R. Surrey, J. Am. Chem. Soc. 77, (1955) 636-654.
[35]. Y. Takeda, K. Yano, T. Kuroki, J. Med. Chem. 40, (1997) 105-111.
[36]. H. R. Shaterian, F. Rigi, Res. Chem. Intermed. 40, (2014) 2983-2999.
[37]. Z. Nasresfahani, M. Z. Kassaee, E. Eidi, New J. Chem. 40, (2016) 4720-4789.
[38]. M. Wang, Y. Liang, Monatsh. Chem. 142, (2011) 153-157.
[39]. A. S. Amarasekara, J. Nguyen, A. Razzaq, J. Polym. Res. 24, (2017) 52-79.
[40]. W. Chen, X. W. Peng, L. X. Zhong, Y. Li, R. C. Sun, Acs Sustain. Chem. Eng. 3, (2015) 1366-1373.
[41]. F. Ghorbani, H. Kiyani, S. A. Pourmousavi, Res. Chem. Intermed. 42, (2020) 2075-2084.
[42]. P. T. Mistry, N. R. Kamdar, D. D. Haveliwala, S. K. J. Patel, Heterocyclic Chem. 49, (2012) 349-357.
[43]. V. K. Ahluwalia, A. Dahiya, Garg, V. Indian J. Chem. 36B, (1997) 88-90.
[44]. J. L. Wang, D. Liu, Z. J. Zheng, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. U.S.A. 97, (2009) 7124-7129.
[45]. Μ. E. A. Zaki, E. M. Morsy, F. M. Abdel-Motti, F. Μ. E. Abdel-Megeid, Heterocycl. Commun. 10, (2004) 97-102.
[46]. N. Foloppe, L. M. Fisher, R. Howes, A. Potter, A. G. S. Robertson, A. E. Surgenor, Bioorg. Med. Chem. 14, (2006) 4792-4802.
[47]. F. M. Abdelrazek, P. Metz1, O. Kataeva1, A. Jäger, S. F. El-Mahrouky, Arch. Pharm. Chem. Life Sci. 340, (2007) 543-548.
[48]. M. M. M. Ramiz, I. S. Abdel Hafiz, M. A. M. Abdel Reheim, H. M. J. Gaber, Chin. Chem. Soc. 59, (2012) 72-80.
[49]. H. Wamhoff, E. Kroth, K. Strauch, Synthesis. 11, (1993) 1129-1132.
[50]. D. Armetso, W. M. Horspool, N. Martin, A. Ramos, C. Seaone, J. Org. Chem. 54, (1989) 3069-3072.
[51]. Y. A. Sharanin, L. N. Shcherbina, L. G. Sharanina, V. V. Zh. Puzanova, Org. Khim. 19, (1983) 164173.
[52]. T. S. Jin, R. Q. Zhao, T. S. Li, Arkivoc xi. (2006) 176-182.
[53]. S. Wang, A. Q. Cheng, Z. L. Zhang, J. S. Li, Synth. Commun. 35, (2005) 137-143.
[54]. N. R. Mohamed, N. Y. Khaireldin, A. F. Fahmyb, A. A. El-Sayeda, Der Pharma Chem. 2, (2010) 400-417.
[55]. H. V. Chavan, S. B. Babar, R. U. Hoval, B. P. Bandgar, Bull. Korean Chem. Soc. 32, (2011) 3963-3966.
[56]. S. B. Mhaske, N. P. Argade, Tetrahedron, 62, (2006) 9787-9826.
[57]. Y. Takaya, H. Tasaka, T. Chiba, K. Uwai, M.-a. Tanitsu, H.-S. Kim, Y. Wataya, M. Miura, M. Takeshita, Y. Oshima, Journal of medicinal chemistry, 42, (1999) 3163-3166.
[58]. Y. Xia, Z. Y. Yang, M.-J. Hour, S. C. Kuo, P. Xia, K. F. Bastow, Y. Nakanishi, P. Nampoothiri, T. Hackl, E. Hamel Bioorganic & medicinal chemistry letters, 11, (2001) 1193-1196.
[59]. R. J. Alaimo, H. E. Russell, Journal of medicinal chemistry, 15, (1972) 335-336.
[60]. M. J. Hour, L. J. Huang, S. C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K. H. Lee, Journal of medicinal chemistry, 43, (2000) 4479-4487.
[61]. H. Li, R. Huang, D. Qiu, Z. Yang, X. Liu, J. Ma, Z. Ma, Progress in Natural Science. 8, (1998) 359-365.
[62]. E. Honkanen, A. Pippuri, P. Kairisalo, P. Nore, H. Karppanen, I. Paakkari, Journal of medicinal chemistry. 26, (1983) 1433-1438.
[63]. A. Baba, N. Kawamura, H. Makino, Y. Ohta, S. Taketomi, T. Sohda, Journal of medicinal chemistry. 39, (1996) 5176-5182.
[64]. M. S. Malamas, J. Millen, Journal of medicinal chemistry. 34, (1991) 1492-1503.
[65]. N. P. Abida, M. Arpanarana, International Journal of Pharmaceutical & Biological Archive. 2, (2011) 1651-1657.
[66]. P. Nandy, M. Vishalakshi, A. Bhat, Indian Journal of heterocyclic chemistry. 15 (2006) 293-294.
[67]. S. Sasmal, G. Balaji, H.R.K. Reddy, D. Balasubrahmanyam, G. Srinivas, S. Kyasa, P.K. Sasmal, I. Khanna, R. Talwar, J. Suresh, Bioorganic & medicinal chemistry letters. 22, (2012) 3157-3162.
[68]. Y. Kurogi, Y. Inoue, K. Tsutsumi, S. Nakamura, K. Nagao, H. Yoshitsugu, Y. Tsuda, Journal of medicinal chemistry. 39, (1996) 1433-1437.
[69]. X. S. Wang, J. Sheng, L. Lu, K. Yang, Y.-L. Li, ACS combinatorial science. 13, (2011) 196-199.
[70]. M. Sharma, S. Pandey, K. Chauhan, D. Sharma, B. Kumar, P.M. Chauhan, The Journal of organic chemistry. 77, (2012) 929-937.
[71]. V. B. Labade, P. V. Shinde, M. S. Shingare, Tetrahedron Letters. 54, (2013) 5778-5780.
[72]. M. R. M. Shafiee, Journal of Saudi Chemical Society. 18, (2014) 115-119.
[73]. A. Shaabani, A. Maleki, H. Mofakham, Synthetic Communications. 38, (2008) 3751-3759.
[74]. S. Rasheed, D. N. Rao, A. S. Reddy, R. Shankar, P. Das, Rsc Adv. 5, (2015) 10567-10574.
[75]. V. K. Rajput, B. Mukhopadhyay, Tetrahedron Lett. 47, (2006) 5939-5941.
[76]. J. Zhang, B. Zhang, J. Zhou, J. Li, C. Shi, T. Huang, Z. Wang, J. Tang, J. Carbohydr. Chem. 30, (2011) 657–662.
[77]. J. Zhang, B. Zhang, J. Zhou, H. Chen, J. Li, G. Yang, Z. Wang, J. Tang, J. Carbohydr. Chem. 32, (2013) 380-391.
[78]. J. F. Zhou, X. Chen, Q. B. Wang, B. Zhang, L. Y. Zhang, A. Yusulf, Z. F. Wang, J. B. Zhanga, J. Tang, Chin. Chem. Lett. 21, (2010) 922-936.
[79]. O. Rosati, F. Messin, A. Pelosi, M. Curini, V. Petrucci, J. Gertsch, A. Chicca, Eur. J. Med. Chem. 85, (2014) 77-85.
[80]. B. Maleki, E. Sheikh, E. Rezaei Seresht, H. Eshghi, S. S. Ashrafi, A. Khojastehnezhad, H. Veisi, Org. Prep. Proced. Int. 48, (2016) 37-44
[81]. S. Roy, K. K. Senapati, P. Phukan, Res. Chem. Intermed. 41, (2015) 5753-5767.
[82]. M. Samadizadeh, S. Nouri, F. Kiani Moghadam, Res. Chem. Intermed. 42, (2016) 6089-6103.
[83]. M. M. Dutta, K. K. Rajbongshi, P. Phukan, Synth. Commun. 47, (2017) 2330-2341.
[84]. M. S. T. Rocha, J. Rafique, S. Saba, J. B. Azeredo, D. Back, M. Godoi, A. L. Braga, Synth. Commun. 47, (2017) 29-298.
[85]. M. Mamaghani, F. Shirini, M. Sheykhan, M. Mohsenimehr, RSC Adv. 5, (2015) 44524-44529.
[86]. F. Ghorbani, H. Kiyani, S. A. Pourmousavi, Current Organocatalysis. 7, (2020) 55-8.
[87]. X. Wang, R. Liu, M. M. Waje, Z. Chen, Y. Yan, K. N. Bozhilov, Chem. Mater. 19 (2007) 2395–2397.
[88]. M. Zhu, G. Diao, Magnetically. 115 (2011) 24743–24749.
[89]. T. Karimpour, E. Safaei, B. Karimi, RSC Adv. 9, (2019) 14343-14351.
[90]. M. Gupta, M. Gupta, Rajnikant, V. K. Gupta, New J. Chem. 39, (2015) 2395-3578.
[91]. S. M. Yuan, J. X. Li, L. T. Yang, L. W. Su, L. Liu, Z. Zhou, Mater. Interfaces. 3, (2011) 705–709
[92]. F. Ghorbani, S. A. Pourmousavi, H. Kiyani, Lett. Org. Chem. 18(1), (2021) 66-81.
[93]. F. Ghorbani, S. A. Pourmousavi, H. Kiyani, Curr. Org. Synth. 17(6), (2020) 440-456.
[94]. F. Ghorbani, S. A. Pourmousavi, H. Kiyani, Current Organocatalysis. 7(1), (2020) 55-80.
[95]. F. Z. Damghani, S. A. Pourmousavi, H. Kiyani, Curr. Org. Synth. 16(7), (2019) 1040-1054.
[96]. S. A. Pourmousavi, P. Moghimi, F. Ghorbani, M. Zamani, J. Mol. Struct. 1144, (2017) 87-102.
[97]. S. A. Pourmousavi, A. Kanaani, F. Ghorbani, F. Z. Damghani, D. Ajloo, M. Vakili, Res. Chem. Intermed. 42(2), (2016) 1237-1274.
[98]. Hoseinabadi, Z. Pourmousavi, S. A. Zamani, M. Res. Chem. Intermed. 42(6), (2016) 6105-6124.
[99]. Fahid, F. Pourmousavi, S. A. J. Sulphur Chem. 36(1), (2015) 16-29.
